Successful Leadership Through Empathy and Trust

“I realized really quick that I thought as a city councilwoman  I could change this community,” she muses with a smile.  “With our city government and how it’s structured, one city council member doesn’t have a lot of decision making power and can be easily overruled.”  That realization put Alyson at a crossroads at the end of her term.  Should she go all in with a political career, maybe running for higher office to have more of an impact, or step back and follow a path in the private sector?  To help light the path forward, Alyson went to her future father-in-law.  A trusted advisor, he had known Alyson since she was 16 and had filled a father role in her life.  “I went to him on the last day to file for the office of mayor and he simply said, ‘Alyson this is the last time I’m going to tell you.  I’ve always believed you have a story to tell and people you can help.  I think we should go into business together.’”  And Alyson went all in.

She spent a year learning her father-in-law’s leadership content and, drawing on her millennial perspective, she helped adapt the content.  Now, seven years later, her father-in-law will joke that he works for Alyson.  She’s developed into a polished keynote speaker, an impactful executive leadership coach and management trainer, as well as a respected published author.  After spending time with Alyson, hearing her content and feeling her heart, no one is surprised that she is doing what she’s doing.  She has found a way to feed her need to give back by helping businesses drive results and helping managers lead with empathy and trust.

WISE partnered with Alyson in 2025 to offer a New and Emerging Manager Training program for its partner member companies.  The inaugural program had 59 professionals registered between two cohort groups.  We’re excited to be partnering with Alyson again to offer this program in 2026.  We had the chance to ask Alyson some questions about her career and common leadership challenges.

WISE:  Alyson, what do you love about what you do?

Alyson:  Without hesitation, it’s helping people achieve greater success and impact.  What I have found is that this is truly not about the stage for me; it’s about the transformation that follows for attendees. That’s what fuels me to keep going. It’s not the spotlight that matters; it’s the impact that matters. And, I stay consistently focused on that.

WISE:  What are the most common leadership challenges you are getting asked about right now?

Alyson:  Hands down, the number one root issue I’m seeing in 2026 – across industries, across team sizes – is a lack of understanding between managers and team members. This shows up every single day, but it’s often hard for people to define. It looks like misaligned expectations. It shows up in poorly handled performance conversations. It surfaces in tension around accountability. It even hides inside “simple” moments like setting a deadline or giving feedback.

Many teams have managers who are trying their best, but they’re not getting the results they want. And when that happens, team members either quit and leave.  Or worse, they quit and stay. They disengage, and that affects everyone.  At the core, we just don’t understand one another. We don’t understand what someone needs from us to feel valued. We don’t understand what someone needs to clearly grasp the expectation and confidently move forward. We don’t understand how to ensure mutual clarity. And here’s the hard truth: most issues with performance, retention, engagement, and turnover are not issues of effort. They’re issues of accuracy. It’s not that people don’t care. It’s that they don’t have the right clarity. When we get that right, success follows.

The second major challenge I see is this: organizations promote strong individual contributors into management roles, but they’re not equipped to drive results through other people.  They’ve proven they can produce results themselves, but, now, they’re responsible for driving results with and through a team,  That’s an entirely different skill set.  Many new managers don’t know how to coach performance, or correctly and strategically identify challenges and opportunities; they don’t know how to systematically empower others;, they don’t know how to delegate in a way that builds ownership instead of dependency. So, unfortunately, they default to either micromanaging, or backing away and hoping for the best.  Leading others requires specific skills.  And right now, that’s the gap many organizations are feeling most.

WISE:  Alyson, you’ve said that the most powerful driving force in business today is change.  What’s the hardest part about implementing change?  Where do people get stuck?

Alyson:  Change is both situational and psychological. Both aspects must be managed. One of the common pitfalls we see teams struggling with when it comes to rapid change is in the implementation phase.  There’s far too much uncertainty about who is responsible for what, to whom, and when, followed by unclear leading and lagging indicators to measure success/failure consistently.  When priorities are unclear and workloads are too heavy, it can easily become a recipe for a more challenging experience for all.  It doesn’t have to be that way, but planning and communication on the front end is key.

WISE:  What differences are there in issues that women and men face in leadership?  Alyson:  One of the biggest differences I’ve seen, across the hundreds of thousands of leaders I’ve worked with, is that many women get in their own way.  Before anyone else questions them, they’ve already questioned themselves.  “I can’t.”  “I shouldn’t.”  “Someone else deserves it more.”  “I’ll never be considered.”  Too many incredibly capable women talk themselves out of opportunities before they ever raise their hand.

Sometimes leadership requires you to lay down the law—with yourself first. To decide you’re moving forward. To choose progress over perfection. Don’t be the person holding yourself back. Mindset work isn’t fluffy; it’s practical. It’s a daily investment to make sure that if anything slows you down, it’s not your own doubt.

WISE:  What advice do you have for new leaders stepping into their role?

Alyson:  The moment you step into a management role, your job changes.  You are no longer responsible only for your own individual results, but rather for the individual and collective results of the team that reports to you.  Your future success will be determined by how successful the people under your leadership become.  That requires a shift in mindset.  You are no longer the star individual contributor.  You are the multiplier.  Your role is to coach, empower, clarify expectations, and remove obstacles so your team can win.  Your individual performance still matters.  But now, it is measured by the growth, execution, and results of other people.  If your team wins, you win.

At the same time, you must become someone the leaders above you want to collaborate with.  Be the person who brings solutions, not just problems.  Be the person who communicates clearly, shares helpful information, and makes their job easier.  Show them what you can accomplish through your team.

WISE:  As we plan for another year of our leadership training with you, Alyson, what are you excited about working with WISE?

Alyson:  One of the things I value most about WISE and this emerging leader program is that you are intentionally including men. You understand that meaningful progress requires all of us working better together. When leadership improves across the board, more women succeed.  More teams succeed. That is how real change happens.

As we move into year two of this program, I anticipate stronger peer relationships, and more engagement with the additional resources on the platform – a great foundation for collaboration that returns dividends throughout careers.

I am also looking forward to seeing the ripple effect over time. One breakthrough idea emerging during a session or a one-off conversation after a meeting can completely shift someone’s trajectory. And a year from now, bringing the first class back to support and mentor new participants has the potential to elevate the entire community. The best is yet to come!

Watch future issues of WISE World for more from Alyson and for information on our 2026 New and Emerging Managers Training.